Vacation rentals in Pittsfield

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Travel insights for vacation rentals in Pittsfield

Use these up-to-date, data-driven insights about booking a vacation rental in Pittsfield including ideal times to book, pricing trends, and more.

What is the cheapest day to stay in a vacation rental in Pittsfield?

The cheapest day to stay in Pittsfield is Wednesday (C$ 229). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is C$ 701.
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Other accommodations in Pittsfield

Find the perfect vacation rental for your stay in Pittsfield. There are 72 hotels in Pittsfield and price data was last updated on 27 August 2025. The average price for a hotel in Pittsfield is .
Hotel on North
Hotel on North

Hotel on North

297 North Street, Pittsfield, MA, United States
0.7 km from city centre
Free Wi-Fi
Parking
C$ 307
Avg. per night
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Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

1350 West Housatonic Street, Pittsfield, MA, United States
5.7 km from city centre
Free Wi-Fi
Parking
C$ 183
Avg. per night
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Fairbridge Inn Express Pittsfield
Fairbridge Inn Express Pittsfield

Fairbridge Inn Express Pittsfield

16 Cheshire Road, Pittsfield, MA, United States
4.1 km from city centre
Free Wi-Fi
Parking
C$ 122
Avg. per night
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Berkshire Inn
Berkshire Inn

Berkshire Inn

150 West Housatonic Street, Pittsfield, MA, United States
1.6 km from city centre
Free Wi-Fi
Air Conditioning
C$ 143
Avg. per night
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Heart OF The Berkshires Motel
Heart OF The Berkshires Motel

Heart OF The Berkshires Motel

970 West Housatonic Street, Pittsfield, MA, United States
4.6 km from city centre
Free Wi-Fi
Parking
C$ 133
Avg. per night
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Where to stay in Pittsfield

Explore different neighbourhoods and areas within Pittsfield to find the perfect location for your stay. Map data was last updated on 27 August 2025.
Navigate to the areas in Pittsfield you plan to visit to find vacation rentals that are close by. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

Facts about staying in Pittsfield

Find useful tips and insights about staying in Pittsfield to help you make the most of your experience. FAQs were last updated on 27 August 2025.

  • How much does a vacation rental in Pittsfield cost?

    Pittsfield vacation rentals are C$ 356/night on average. However, you may find that prices fluctuate depending on the time of year. For example, May is the most expensive month to book a vacation rental in Pittsfield, and February is often the cheapest month to book. Recently, our users found rentals for C$ 56/night - which is currently the cheapest price. Keep in mind that anything C$ 332/night or less is still considered a good deal.

  • Are there any Motel vacation rentals in Pittsfield?

    Yes, there are 5 Motel vacation rentals in Pittsfield. According to our data, Heart OF The Berkshires Motel is currently the most popular Motel rental in the city.

Find better results for your stay in Pittsfield

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